


Pride

by wigglebox



Series: Post-Season 15 Supernatural Fics / pre-finale [7]
Category: Supernatural
Genre: Drunken Shenanigans, Gay Pride, HIV/AIDS, Homophobic Language, Human Castiel (Supernatural), M/M, Pride, Sad with a Happy Ending, Slurs
Language: English
Status: Completed
Published: 2019-06-15
Updated: 2019-06-15
Packaged: 2020-05-12 12:52:59
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,215
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19229527
Author URL: https://archiveofourown.org/users/wigglebox/pseuds/wigglebox
Summary: AKA: Four times Dean Winchester stumbled across Pride celebrations, and one time he made his own.





	Pride

1

The first time Dean experienced a Pride celebration, he was thirteen years old and they were in Boston tracking down a pretty malevolent ghost. Ghosts weren’t uncommon in a city with old bones but this one was particularly nasty, woken up by a construction project in North End. 

His father left him in a shitty hotel on Stuart Street, a block and a half away from Boston Common. Dean was grumpy and annoyed he couldn’t go along with his father when the previous week, he was encouraged to. John mentioned something about it being ‘too dangerous now’, and Dean obeyed him, but still seethed in silence. He didn’t even have his brother to entertain him since Sam was still in South Dakota, overcoming a bought of the flu.

Hot, bored, and antsy, Dean flipped from station to station on the TV, finding nothing but talk shows and some reruns of The Andy Griffith Show. Dean hated being left behind, even if it was “for his own safety”. He was thirteen, he could handle shit himself. 

After accepting the fact there weren’t any premium Skinamax channels, Dean threw the remote onto the other bed in a huff, watching it bounce off and land on the floor. He could feel the sweat starting to form on his forehead and under his shirt. Summer was the worst season, and Dean didn’t think they should pay for a room without air conditioning. 

The heat and stale air only furthered Dean’s bad mood until he couldn’t take it anymore.

He scribbled a quick note about going down to the store for ‘some stuff’ and left it on the desk, just in case his father came back early. Dean threw the pen down, grabbed the room key, and slammed the door behind him. 

As soon as Dean left the hotel lobby, he was swept up in a crowd of people, most of them walking in one direction. It was a strange group of people, most looking like college students with the odd old person trying to cling onto the hippie lifestyle of their youth. It seemed like an eclectic sea of people, and Dean found himself following them like a school of fish to wherever they were heading. 

A short walk later, Dean found himself on the south side of Boylston Street, people cheering and chanting all around him. The view was blocked by the adults in front, and Dean tried to push himself through to the front. It seemed like a parade. There was a parade? What national holiday was there in June? None, as far as Dean was concerned. 

Dean finally managed to scoot in front of two women who had their arms around each other and were laughing but also chanting: _Pride is Power! Pride is Power!_

The crowd made the air even hotter and stickier, but Dean put his discomfort aside and focused instead on reading the banners that were traveling down the street in front of various groups. Some banners had rainbows while some were just sheets with spray painted words. There were old cars, not unlike his father’s, that had rainbows painted on them with rainbow flags protruding from every direction. There were women, and men, standing in these cars and the backs of trucks. They were also colorful, some wearing makeup, some in plain t-shirts but waving the flags enthusiastically. Dean knew the highly made-up women were drag queens -- he had seen them in New York City three years prior. They were nice to him then, even if their makeup scared him. 

Dean watched as car, truck, and groups marched by. One banner read “Irish-American Gay, Lesbian, and Bisexual Pride”, others were spray painted with “God made us Queer!” and “Love!” in rainbow colors. There were also a few banners that sobered the crowd but didn’t stop them from reacting. The one that drew the most noise, more anger than celebration, was one that seven people were holding while marching in silence. The words weren’t spray painted, and the bright red letters stood out against the black background: “EVERY SEVEN MINUTES, SOMEONE DIES OF AIDS”. A banner right behind it read: “AIDS: WE NEED RESEARCH, NOT HYSTERIA!”

They were the harshest out of the rest of the celebration, but Dean didn’t understand it in full. He had seen on various newscasts reports of AIDS throughout the years on diner and motel TV’s, but John would sniff and say it was the “Queers’ fault. Doesn’t affect us in the slightest,” and changed the channel.

The black banners turned the corner to go up the street that split the Boston Common from the Public Garden and soon, all the cars, floats, and trucks once again filled the space with laughter, music, and cheering. 

Dean, however, felt the mood sour for him. 

He withdrew from his position on the sidewalk, out of the crowd, and back down another street looking for a quick bite to eat. Dean decided to never tell his father about the parade of ‘Queers’. 

 

2

The second time Dean stumbled across Pride was six years later. Dean found himself back in New York state with his father and brother. There was a rash of parents going missing in, of all places, Sleepy Hollow. 

Several days, and a few Changeling deaths later, they had one last night in the town before heading out of town, going wherever John wanted them to go. School was out, so -s was there, but he wasn’t a joy to speak with. Dean could feel growing resentment radiating off of his brother, and it wasn’t fun to be around. It made Dean feel uneasy.

That night, when everyone fell asleep, Dean lifted the keys to the Impala out of his father’s jacket and slid out the door as quietly as he could. Dean shifted the car into neutral and let it to slowly back away from the building without turning on the engine until he was far enough away. 

Dean wanted to go to New York City. 

He wasn’t naturally city inclined, but he had spent most of the winter months holed up in a mountain cabin in Wyoming with only his father for company. After the spring thaw, and after Sam was let out of school in early June, they’d been roaming back roads only. Dean craved to see a building that wasn’t a school, church, or a post office. Even a street light would be welcomed.

Dean had only been to Manhattan once, back when he was ten and was greeted by the nice drag queens hanging outside of the club next to the motel. They hit on his father, and his father wasn’t happy about it. Dean figured it was because their makeup was scary. 

Dean followed I-87 farther south than expected and had to get off on the Kennedy Bridge, throwing a toll at the attendant. The city was a grid so it shouldn’t have been too hard to work out but Dean remained on FDR Drive for a while, circling the island. At some point in the drive, Dean realized he didn’t have a map. 

Finally, as Dean began his ascent back north, he decided to make a break for it at 11th Avenue. 

A couple turns later, he found himself in the same neighborhood, on the same street where they stayed in back in 1989. The fleabag motel looking the same with the crumbling brick exterior and rust stains running down underneath the narrow windows. But, since that time, many more clubs and shops opened up around it with neon signs and colorful posters plastered in the window.

Dean’s watch read 11:45 p.m. but the street was still kicking with life, and all of the brightness and color to keep a man awake for hours. Rainbow flags, men and women walking together up and down the street, pausing to laugh with others and hug them or kiss them on the cheek. The neon lights illuminated bar windows, and Dean could hear music pulsing up and down the block. 

It was almost the exact opposite of an old country road. 

Dean parked on a nearby side street and walked almost guiltily back into the crowd, hands shoved in his pockets. He felt underdressed with his jeans and a basic shirt, but his curiosity made him travel on.

The first stop was that dirty motel, just for nostalgia. Dean passed several groups of men and some women who were laughing, holding drinks out on the sidewalk. They acknowledged him with some wariness -- a stranger among them. Dean didn’t blame them. He didn’t match the vibe. 

The motel was still open for business and looked just like it did inside as it did a decade ago from what Dean could make out through the windows. It seemed highly out of place in this land of gayness and color. Did his father realize where he decided to stay? Dean wasn’t the best with the history but he knew that this area of the city has always been home to those ‘queers’ that his father sneered about.

“They won’t let you up there unless you have someone with you.” 

Dean spun around and saw a drag queen smoking a cigarette over by the curb of the sidewalk. She had platform, white pleather boots on, a hot pink and banana yellow mini-dress reminiscent of the ’60s, and hair that seemed as high as the Empire State Building. Her make up was just as exaggerated as Dean remembered, if not a little more chaotic. It wasn’t as scary as he remembered, though. 

“I’m not looking for a room. I’m just -- just looking I guess.”

The queen smiled and blew more smoke into the air. It wasn’t a cigarette - it was a joint. 

“That’s what they all say. If you really want to get your rocks off, head over to Hanging Gardens - there are a few guys left who still have their adrenaline up after the parade today.”

Dean felt himself blush and looked away. 

“I don’t swing that way. Sorry,” Dean lied. It was a truth he didn’t want out. He certainly didn’t have the confidence to stroll into a night club and pull a random man into a motel just for sex. Women, not a problem. With men, he was always more selective, and discrete. If his father found out about any of it -- 

The queen raised an expertly painted eyebrow before a smirk grew from the corners of her mouth. 

“People who don’t swing that way don’t find themselves here in the middle of the night during Pride. Maybe you just have some discovering to do,” she said, voice mystical and slightly hoarse from the smoke. She inhaled, then exhaled a large haze of smoke. Dean watched it dissipate in the air. 

“I was just driving around.” 

“Mmhmm, that’s what they always say.”

The queen flicked the end of her joint into the street and straightened herself out before offering an arm to Dean. 

“Come on in and see a show, honey. It won’t hurt. I wouldn’t want you coming all this way for nothing.”

And because he had nothing else to say, and nowhere else to go, Dean followed. 

 

3

The third Pride-related something Dean happened upon was in California. 

He went to Palo Alto to try and talk to Sam after a near year of radio silence. That year was cold, silent, and rough. John went off on his own more and more, leaving Dean alone without anything to do, and no guidance. Sometimes, Dean would stumble across a case, or his father would leave one on the coffee table when he left. Those cases never lasted more than a day and didn’t get Dean’s adrenaline pumping. 

But the Impala was officially his now.

John left three days prior, mumbling about something happening out in Oklahoma and took the truck he ‘borrowed’ without answering any questions from Dean. 

Dean was an adult now, it’s not like it should have hurt all that much, but he did hate being alone. Drinking alone was bad, thinking alone was bad --

The silence was bad. 

For months, Dean had debated traveling to California to see Sam again. The night his brother left was quite possibly the worst night of his life apart from their mother dying. On some days, Dean found himself angry, frustrated at Sam’s lack of empathy for his own family and all the work they’ve done. But then on other days, Dean was jealous that Sam managed to get out and clearly planned an escape for years. 

Most days, he was just sad that Sam didn’t think Dean would want to go too. 

But now, as Dean sat in the sterile motel room in Klamath Falls, he realized he was only a six-hour drive away from Stanford, and he could be there by late afternoon.

Dean didn’t give himself the chance to overthink his decision as he grabbed the keys, checked out at the front desk, and took off down I-5. 

Turned out it was all for nothing. 

Dean had forgotten that colleges let out at the beginning of May instead of mid-June. 

Sam was in a dorm and had no apartment address Dean could find. His cell phone also changed. Dean didn’t know Sam’s friends, his new hang out spots, or where the kid may have gone for summer break. 

Instead of abandoning the plan right away, Dean sat at a nearby cafe that summer students flocked to. He hoped he blended in, but still felt self-conscious he didn’t have a laptop or a group of friends around his table. The chances of seeing Sam there was slim to none, just due to the sheer size of the place, but he wanted to feel like he did something to find his brother. 

An hour later, Dean was bored and people were looking at him weird. He eventually abandoned his spot and went back to the car, trying not to let the disappointment build too much, too fast. 

Dean remembered in a postcard (the only one Sam sent to him) that he liked a local bar since they let him drink even if he wasn’t 21. Dean threw the car into gear and wove up and down the nearby streets until he found it. 

Dean stayed there for three hours but left before the crowd really got going. The spirit and energy he had to meet up with Sam had faded, and now he was just grumpy and annoyed with himself for thinking that showing up in a city without any notice would work. 

He pointed the Impala in a direction and floored it. Dean didn’t know which way he was going, and it didn’t really matter. It’s not like he was heading to meet anyone, see anyone, or be with anyone. 

Nearly forty-five minutes later, Dean wound up in downtown San Francisco.

He pulled off the main road to find a place to stay for the night. He felt that creeping numbness in the ends of his fingers which would soon radiate up his arms and make him feel like trash for the night. That was the indicator to get boozy. 

A small hotel off Market Street had a vacancy, and Dean rolled up, shelling out most of what he made last week in a game of pool for a one night stay. As Dean walked over to the elevator, seeing if he missed any calls on his phone, he completely missed the Pride flags, bulletin board notices, and some couples or groups of people milling about in the lobby. No one noticed him either. 

Dean later woke from a two-hour snooze and decided that it was time for the alcohol to start flowing. There were some promising bars on his way into the city and Dean wondered if he could walk them instead of having to fit his car onto the narrow side-street parking. 

Down in the lobby, he was given a walking map of The Castro, the district he was currently in, and it highlighted the best bars and restaurants in town. 

“I recommend Eden if you want food, or Myner Wyne if you want more booze than food,” the front desk clerk said, pointing to two dots on the map. They were walkable, and Dean decided to go with more booze than food. 

He thanked the kid at the desk and headed out, still oblivious to his surroundings. 

 

An hour later, he was smashed. 

Not a good smashed either, but the kind where he should have just bought the alcohol from a store and stayed in his room.

Dean did head to the bar on the map at first, but soon after sitting down, he realized it was more of a hoity-toity bar than one where he’d be more welcomed. Dean stayed for a quick drink, then sauntered out in the hopes to find an actual dive bar. The desire for the lowest of the low was knocking at the back of his head since that’s how he felt. 

A block away, Dean found his destination. 

The place was nothing more than a hole in a wall, seedy looking place simply called “Harry’s” that was tucked between two clothing stores. It was away from the main thoroughfare, and not a bright beacon of fun. Just what Dean wanted. 

It turned out it wasn’t as dive-y as he wanted but it suited him just fine. The patrons were all men and no one was dancing or shouting like the other place. They also all wore a lot of leather, and some didn’t wear shirts, but Dean didn’t think about it. All he wanted was drinks. Drinks, drinks, alcohol, booze, get-me-fucked-up please as his mood soured the more he thought about where he was supposed to go after this failed family visit. 

It was just as Dean tumbled over the cliff to Shitfaced did he finally realize where exactly he wound up. 

It was a leather bar. 

He was in god damn fucking _San Francisco_ of _course_ he’d wind up here. In his rapidly deteriorating state, Dean finally saw the flags hanging on the wall next to dozens of pictures. There were some posters for a drag night, and others for a leather party for the 4th of July. A poster closer to Dean advertised PRIDE CELEBRATION! JUNE 26-27th with a list of details and a small map that he couldn’t figure out because now the bourbon was hitting. 

Of course it was Pride. It was always Pride. Every time it was Pride Dean found himself at some major city. It was like the Universe was playing a stupid joke. 

Another drink down, another requested, and Dean slipped further into the hole. 

At some point in the night, Dean was approached by a man who was technically wearing a shirt, but it clung so tightly to his muscled body that it looked painted on. The stranger was also wearing tight leather pants, in theme with the bar.

“You know, usually I kick people out of my bar for not adhering to the rules but I may just make an exception for you,” the man said, his voice low and deep but still discernible over the music. Dean looked down at his jeans and shirt, shrugged, and drank the last of his bourbon. The stranger was older with some gray peppered into his light brown hair and a small tan colored his face. Laughter lines were visible around his eyes which were a deep, dark brown. 

He looked nice. 

“And why exac’ly am I an’ception?” Dean asked, wanting to hear the man speak again. 

The stranger smiled at the slurred words and sat down on a stool next to Dean. He was so close, Dean could feel his body heat. 

“I’d like to show rather than tell,” the man teased, his kind smile turning into a teasing smirk, “My hands are better than my words.”

Dean mimicked the teasing expression but didn’t say anything. The man wasn’t trying very hard, but Dean didn’t need an effort that night. 

Fuck it, right? It’s Pride. Time to take Pride in himself for being so -- 

Whatever he was. 

Pride-ness and rainbows. Time to literally fuck it. 

The rainbows followed him through the bar, guiding him and the stranger through the crowd, through a back hallway, out the back door, and into the back alleyway. 

It was all so colorful until it was suddenly very dark. There were no streetlights back there, and the smell of people and alcohol completely evaporated. 

The stranger pressed himself up against Dean, covering his mouth with his own. Dean was sloppier, but the man, stranger, ?owner?, didn’t seem to care. 

The man, stranger, owner of Harry’s -- probably Harry himself, started to let his hands wander as he kept Dean captured by the mouth. It felt good. It wasn’t _great_ , Dean had better hook-ups with men than this, but it was good enough for the moment. 

Dean allowed the man probably-called-Harry to feel him up under his shirt, over his chest, down his back, and even finger the waistband of his pants all the other hand was moving against the jeans covering his ass. The movement caused Dean’s hips to move closer to Harry’s (???) groin and the very present hard-on there already. Dean dug his own fingers into Harry’s waist and allowed the man to break free from the kiss, and move alongside his jaw and neck. A typical routine for a hook-up, but this time, Dean really felt nothing. No blood flow at all. Nothing, nada, zip, not even a hint of something: Nothing. Dean still felt numb, and if anything, the alcohol made it worse.

Harry stopped suddenly and pulled his head away, fingers dancing over a scar Dean had on his ribcage. 

“What’s this from? Feels large.”

Dean shrugged, leading his head against the brick behind him while loosening his grip on Harry’s waist. The small iota of a mood that was building between them was already dissolving.

“Scar. Got a few,” he mumbled. 

Harry frowned and used both his hands to lift Dean’s shirt up, just enough to expose everything under his shoulders. He knew there were still at least two big bruises from last week’s hunt on his right side and the left side of his waist. There was that scar Harry already found (Dean couldn’t remember where that came from), and several more on his waist where a shapeshifter slashed at him a few times with a knife. There were other little scars and bumps here and there that weren’t too significant, but apparently captured Harry’s interest.

“Just hazards of th’job,” Dean slurred, closing his eyes. He didn’t care if he slept or fucked but he wanted to lay down somewhere. Things were spinning. 

“What exactly do you do?” Harry asked, lowering Dean’s shirt and stepping away, out of Dean’s space. Dean shivered in the cool, San Francisco night air that cascaded over him. 

What did he do? Yes, what did he do -- that was a good question. Right now, he was trying to get done by this beefy man standing in front of him who was sexy but not in like, a GQ kind of way. What did Dean do? Before this, he was trying to find his brother but didn’t put that much effort into it, already knowing it wouldn’t work. Before _that_ \-- where was he again? Oregon? Oregon, yes. 

“Kill things,” was all Dean could get out of his fuzzy brain as thoughts blurred together. 

The silence lasted long enough for Dean to open his eyes, trying to focus on Harry. Harry had a look of fear and confusion on his face and had retreated back a couple more steps.

“Hunting. Thas’what I mean,” Dean tried to explain, but all that did was morph Harry’s face from fear to revulsion. 

“I’m a vegetarian.” 

Dean snorted, closing his eyes, “Of course you are.”

He wasn’t getting laid that night. 

 

Somehow, Dean made it through the bar and down the street without being hit by a car, and back to the hotel. He fell on top of the bed, fully clothed, and slept past his check-out time the next day. 

4

The fourth time Dean found himself in a Pride celebration was in Pittsfield, Massachusetts. 

There was a witch somewhere in Hinsdale, a neighboring town, and the three of them concluded she had to have been somewhere up in the surrounding Berkshires after fleeing a murder charge in 1876.

It was nearly a year after Chuck unleashed hell back into the world, and there was still cleaning up to do. It was easier now that Heaven and Hell were locked up with the exceptions of intake, but it was still a difficult job. There were more hunters springing out of the woodwork now, and Dean was grateful for their help. 

It was also a hard adjustment for Cas. Jack had asked him if he wanted to stay where he was or go back to Heaven before it closed. Cas decided in the end to stay but knew his grace was needed to help rebuild the chaos that Heaven had become. Jack, in good faith, lef Cas with some small power to heal wounds. It wasn’t in a miraculous “The Blind Shall See!” kind of way, but more of a “no more scars or bruises” kind of sense. 

Cas struggled with human things, even a year later. His previous experience wasn’t long enough to help him how. But, Cas still helped. Both Dean and Cas didn’t talk about The Decision, but Dean knew the moment was building where everything would spill eventually. It was like staring down an oncoming train. 

On the second day in Hinsdale, they realized they had to go to Agnes’ original home in Pittsfield, just over the line. The home search lead them to the library because when does it not.

As they drove onto East Street, they hit a wall of barriers, and that’s when Dean noticed the rainbow flags dangling from the street lights. There was a festival up ahead at Park Square, a little roundabout park, and they closed the streets for the block party. 

Sam managed to guide them to a close enough parking lot, but they still had to maneuver through the crowds to get to the library which was on the edge of the celebration.

Before they got to the library steps, Sam spun around suddenly and pointed to a building across the way. 

“We need the court records for her murder trial. You may as well try to break in now while there’s a distraction,” he instructed. 

Dean rolled his eyes. He didn’t feel like trying to swim the Big Gay Sea but knew Sam was right. They were least likely to get caught now. 

Dean turned to Cas who had his back to them, watching the crowd.

“Do you want to read some books or help me commit a felony?” 

Cas glanced at Dean before staring back at the crowd, “I’ll stay here. I think you can get it done faster on your own.” 

Dean made for the courthouse by himself, squeezing past various people: dancing groups of friends, couples kissing next to other couples kissing, and others who were alone but still ready to party (and smoke some weed). 

Dean wanted to grab up any time alone he could with Cas, and had to hide his frown of disappointment at Cas’s choice. The alone time together made it easier for Dean to practice in his mind what he’d say when the time came. If the time ever came. 

As Dean passed a couple making out at the curb of the sidewalk, he threw them a sneer of jealousy before disappearing into the shadows of the building. 

Forty minutes later, Dean finally emerged with the records in hand. They were old so they weren’t on a computer system, and Dean found himself cursing the Pittsfield way of organizing things. 

When he emerged, the crowd had dwindled in his area, moving more towards the center traffic island. 

He stood outside on the sidewalk, watching as people still danced, kissed, touched, and all around celebrated themselves. The pang of disappointment and jealousy from before started to grow again, and Dean found himself biting the inside of his lower lip in frustration too hard. 

Movement out of the corner of Dean’s eye caught his attention, and he saw Cas and Sam emerging from the library. Sam was talking to someone on the phone, descending the steps while Cas stayed at the top, watching the same crowd as Dean.

Now Dean’s attention was completely focused on one person. It was the little moments that Dean stored away in his mind to help mitigate the torture of having to keep everything to himself. It was the little moments that helped remind him that waiting was vital, and that he couldn’t be selfish. It was the little moments like now as the sun began its descent to the horizon, and a golden light partially illuminated Cas from the top down that made Dean smile to himself. Dean always looked when he could during the little moments. 

This time, however, Cas looked back. 

5

In the end, Pride was never something Dean could immerse himself in. He knew it made others happy, but it was never anything that he could relate to on a personal level. Not that Dean wasn’t proud of himself, or whatever Pride meant, and not that he didn’t support The Struggle, but he always felt like the odd one looking in. He didn’t know what to call himself, and he didn’t care to. It wasn’t his world, and never would be. 

Thirty-two years after Dean experienced his first Pride on that hot, sticky day by the Boston Common, he found himself back there, only this time he wasn’t alone. 

Dean and Cas were in Boston for a small case involving some creature living in the hidden basement of a recently renovated college dorm. Sam would be joining them the next day as he finished his own job in Louisiana with Eileen, giving Dean and Cas twenty-four hours to themselves. 

They could hear the parade and celebration from their room in a small hotel on Stuart Street that finally fixed the air conditioning and put down some new carpet. They cracked the window open as far as they could, a cool breeze carrying the celebration to them. The cheers and chants mixed with their own noises that exclusively belonged to them. 

Movement was scaled down from a street level to a bed level: bodies pressed against each other, elevated heart rates, rushing adrenaline, and flushed cheeks as Cas and Dean marched to their own, private beat. The only heat Dean felt was the one between him and Cas, hot skin sliding against hot skin.

There were colors, many of them, as Dean felt bolts of pleasure rock through his body, causing him to squeeze his eyes shut. The color from the rainbows that littered cities and towns during the month of June faded together into a bright white light, Dean chanting his own quiet demands and wishes to the person above him. 

Dean’s Pride celebration had finally come.

**Author's Note:**

> Hello!  
> It's Pride month and I wanted to write a little something with my favorite disaster bisexual character.  
> Please note: my writing Dean as not wanting to label himself is me not trying to erase his bisexuality - just trying to think about how he would think about it.
> 
> Two small easter eggs: Hanging Gardens is in reference to the city of Babylon. Babylon was the name of the main gay club in the show 'Queer as Folk'. Yes, I named the witch Agnes after Agnes Nutter from Good Omens.
> 
> This is LIGHTLY EDITED so if there are any egregious grammar or spelling errors (outside my own style of writing) please let me know! 
> 
> Tumblr: Wigglebox


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